That Guy with the Glasses is a website that showcases original entertainment for an audience including video game enthusiasts and movie buffs. It primarily stars Chicago native Douglas Darien "Doug" Walker (born November 17, 1981) aka "That Guy with the Glasses". The founder and administrator of the site is Michael Michaud, in addition to being the CEO of the parent company Channel Awesome. The site was launched in April 2008 after the original videos were removed from YouTube following complaints of copyright infringement.

The website is home to several episodic series, starring Douglas Walker and others. The main Douglas Walker series are 5 Second Movies (hyper-edited feature films), The Nostalgia Critic (reviews of 1980-90s films and television), Ask That Guy with the Glasses (comedy question and answer show) and Bum Reviews with Chester A. Bum (plot summaries of current feature films). Other videos and written articles are hosted on the site, including some minor series and sketches starring Walker. Videos are now hosted by blip.tv after problems with earlier provider Revver.

Douglas Walker's first appearance on the web was on the video website YouTube, in which he created satirical video reviews of films and other media entertainment of the past and present. The series drew complaints from major studios like 20th Century Fox and Lions Gate over alleged copyright infringement. This led to his video content being taken off the website. Walker attempted to re-upload his content by assigning each video a new, separate channel so that if one were deleted, the others would be left intact. However, due to continuing issues with Youtube, Walker decided to leave the website altogether and create the website That Guy with the Glasses with Internet webmaster Mike Michaud. Michaud had created the sites' parent company, Channel Awesome, after he and two others were laid off from Circuit City in 2007. Michaud has stated, "If we didn't lose our jobs, [the business] wouldn't have happened anytime soon."

The site was re-launched in April 2008, and all of Walker's future videos would only be posted there. The site later expanded to feature content from various other contributors. In December 2008, Walker appeared in a commercial for the PBS documentary Make 'Em Laugh: The Funny Business of America, performing a series of brief imitations of famous comedians, from Charlie Chaplin to Stephen Colbert. In 2009, Doug and Rob Walker and Brian Heinz produced an iRiff of The Lion King for RiffTrax. In March 2009, the iRiff was chosen as the winner of the website's RiffTrax Presents contest. The performers received $1,000 and, with instruction from Michael J. Nelson, Kevin Murphy and Bill Corbett, recorded a commentary for the film Batman Forever.